ChemicalBook CAS DataBase List Benzene, 5-ethynyl-1,2,3-triMethoxy-

Benzene, 5-ethynyl-1,2,3-triMethoxy- synthesis

8synthesis methods

Product Name:Benzene, 5-ethynyl-1,2,3-triMethoxy-
CAS Number:53560-33-1
Molecular formula:C11H12O3
Molecular Weight:192.21

86-81-7 Synthesis

86-81-7
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Dimethyl (1-Diazo-2-oxopropyl)phosphonate

90965-06-3
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53560-33-1
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Yield:53560-33-1 99%

Reaction Conditions:

with potassium carbonate in methanol;

Steps:

1 General procedure for the synthesis of arylalkynes (11)

K₂CO₃ (4.15g, 30mmol) was added to the stirred solution of corresponding benzaldehyde (15mmol) and 1-diazo-2-oxopropylphosphonate (3.69g, 18mmol) in dry methanol (55mL) at 0° (ice-water bath).⁷⁰ The reaction mixture was stirred overnight in ice-water bath, then methanol was evaporated, and the residue was dissolved in 15mL of cold water. The precipitate was filtered off, washed with water, and dried in vacuo to yield arylalkyne as colorless crystals. The targeted arylalkynes 11 were used without further purification.

References:

Demchuk, Dmitry V.;Samet, Alexander V.;Chernysheva, Natalia B.;Ushkarov, Vladimir I.;Stashina, Galina A.;Konyushkin, Leonid D.;Raihstat, Mikhail M.;Firgang, Sergei I.;Philchenkov, Alex A.;Zavelevich, Michael P.;Kuiava, Ludmila M.;Chekhun, Vasyl F.;Blokhin, Dmitry Yu.;Kiselyov, Alex S.;Semenova, Marina N.;Semenov, Victor V. [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 2,p. 738 - 755]